US8067103B2 - Optical articles with thin hydrophobic layers - Google Patents
Optical articles with thin hydrophobic layers Download PDFInfo
- Publication number
- US8067103B2 US8067103B2 US11/895,484 US89548407A US8067103B2 US 8067103 B2 US8067103 B2 US 8067103B2 US 89548407 A US89548407 A US 89548407A US 8067103 B2 US8067103 B2 US 8067103B2
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- US
- United States
- Prior art keywords
- groups
- perfluorinated
- group
- substrate
- organometallic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
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- 230000003287 optical effect Effects 0.000 title claims abstract description 25
- 230000002209 hydrophobic effect Effects 0.000 title description 15
- 239000000203 mixture Substances 0.000 claims description 27
- 239000000758 substrate Substances 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 22
- 238000000576 coating method Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 19
- 150000002430 hydrocarbons Chemical class 0.000 claims description 16
- 150000004703 alkoxides Chemical class 0.000 claims description 15
- 125000002524 organometallic group Chemical group 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Chemical group 0.000 claims description 7
- 239000011574 phosphorus Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 229920000307 polymer substrate Polymers 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 25
- 239000002344 surface layer Substances 0.000 abstract description 6
- 230000005661 hydrophobic surface Effects 0.000 abstract description 3
- -1 polyethylene terephthalate Polymers 0.000 description 18
- 239000010410 layer Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000003085 diluting agent Substances 0.000 description 13
- 150000002902 organometallic compounds Chemical class 0.000 description 12
- 229920000515 polycarbonate Polymers 0.000 description 12
- 239000004417 polycarbonate Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000001298 alcohols Chemical class 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000010936 titanium Substances 0.000 description 9
- 238000007654 immersion Methods 0.000 description 7
- 229920001296 polysiloxane Polymers 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920001410 Microfiber Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 150000003009 phosphonic acids Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 229910052726 zirconium Inorganic materials 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229940052303 ethers for general anesthesia Drugs 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 229910021481 rutherfordium Inorganic materials 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 150000001860 citric acid derivatives Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000000126 substance Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical group C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
- DMLWITSKISPJIJ-UHFFFAOYSA-N 2-ethylhexan-1-olate Chemical compound CCCCC(CC)C[O-] DMLWITSKISPJIJ-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- 0 C*C([Y])CF.CCOCC([Y])CF Chemical compound C*C([Y])CF.CCOCC([Y])CF 0.000 description 1
- CLBACUJXLGWVQB-UHFFFAOYSA-N CC#CC1(CC)CCC1C Chemical compound CC#CC1(CC)CCC1C CLBACUJXLGWVQB-UHFFFAOYSA-N 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N CC(=O)C(C)C Chemical compound CC(=O)C(C)C SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N CC(C)=O Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- VFAMWAQOWFZHHV-UHFFFAOYSA-N CC[Y] Chemical compound CC[Y] VFAMWAQOWFZHHV-UHFFFAOYSA-N 0.000 description 1
- UGAGAPJTEYFXPJ-UHFFFAOYSA-N COP(C)(C)=O.CP(C)(C)=O.CP(C)(C)=O Chemical compound COP(C)(C)=O.CP(C)(C)=O.CP(C)(C)=O UGAGAPJTEYFXPJ-UHFFFAOYSA-N 0.000 description 1
- LRMLWYXJORUTBG-UHFFFAOYSA-N CP(C)(C)=O Chemical compound CP(C)(C)=O LRMLWYXJORUTBG-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- HSHIKMZZBQISIH-UHFFFAOYSA-N OCCCC[Y] Chemical compound OCCCC[Y] HSHIKMZZBQISIH-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- HSXKFDGTKKAEHL-UHFFFAOYSA-N tantalum(v) ethoxide Chemical compound [Ta+5].CC[O-].CC[O-].CC[O-].CC[O-].CC[O-] HSXKFDGTKKAEHL-UHFFFAOYSA-N 0.000 description 1
- LLZRNZOLAXHGLL-UHFFFAOYSA-J titanic acid Chemical compound O[Ti](O)(O)O LLZRNZOLAXHGLL-UHFFFAOYSA-J 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/18—Coatings for keeping optical surfaces clean, e.g. hydrophobic or photo-catalytic films
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/06—Coating with compositions not containing macromolecular substances
- C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
- G02B1/14—Protective coatings, e.g. hard coatings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B27/00—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00
- G02B27/0006—Optical systems or apparatus not provided for by any of the groups G02B1/00 - G02B26/00, G02B30/00 with means to keep optical surfaces clean, e.g. by preventing or removing dirt, stains, contamination, condensation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/46—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen
- C08G2650/48—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing halogen containing fluorine, e.g. perfluropolyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/08—Cellulose derivatives
- C08J2301/10—Esters of organic acids
- C08J2301/12—Cellulose acetate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2471/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/31536—Including interfacial reaction product of adjacent layers
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T428/31544—Addition polymer is perhalogenated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31681—Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31728—Next to second layer of polyamide
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- General Physics & Mathematics (AREA)
- Surface Treatment Of Optical Elements (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
- Eyeglasses (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/895,484 US8067103B2 (en) | 2006-08-24 | 2007-08-24 | Optical articles with thin hydrophobic layers |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83980906P | 2006-08-24 | 2006-08-24 | |
| US11/895,484 US8067103B2 (en) | 2006-08-24 | 2007-08-24 | Optical articles with thin hydrophobic layers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20080049326A1 US20080049326A1 (en) | 2008-02-28 |
| US8067103B2 true US8067103B2 (en) | 2011-11-29 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US11/895,484 Expired - Fee Related US8067103B2 (en) | 2006-08-24 | 2007-08-24 | Optical articles with thin hydrophobic layers |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US8067103B2 (fr) |
| WO (1) | WO2008024475A2 (fr) |
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| WO2015042488A2 (fr) | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Procédé permettant d'empêcher l'encrassement sur une surface métallique à l'aide d'un agent de traitement de modification de surface |
| WO2015042486A1 (fr) | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Composites destinés à être utilisés dans des opérations de stimulation et de contrôle de sable |
| US9060560B2 (en) | 2007-08-10 | 2015-06-23 | Greenhill Antiballistics Corporation | Composite material |
| US9328788B2 (en) | 2010-10-18 | 2016-05-03 | Greenhill Antiballistics Corporation | Gradient nanoparticle-carbon allotrope-polymer composite material |
| US9421574B2 (en) | 2013-03-18 | 2016-08-23 | Aculon, Inc. | Fluorocarbon polymer coatings prepared by living polymerization |
| WO2016145263A1 (fr) | 2015-03-10 | 2016-09-15 | Baker Hughes Incorporated | Procédé de pompage d'un agent de traitement de modification de surface contenant un fluide aqueux dans un puits |
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| US9994732B1 (en) | 2014-09-12 | 2018-06-12 | Steven Martin Johnson | Polysilazane and fluoroacrylate coating composition |
| US10039442B2 (en) | 2014-02-07 | 2018-08-07 | Sur-Seal Corporation | Anti-fog film for an endoscope |
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| US10562065B1 (en) | 2015-11-03 | 2020-02-18 | Newtech Llc | Systems and methods for application of polysilazane and fluoroacrylate coating compositions |
| US10584264B1 (en) | 2016-02-25 | 2020-03-10 | Newtech Llc | Hydrophobic and oleophobic coating compositions |
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| US20070275174A1 (en) * | 2006-05-24 | 2007-11-29 | Hanson Eric L | Fishing fly and fly fishing line with fluorocarbon coating |
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| US8178004B2 (en) | 2008-06-27 | 2012-05-15 | Aculon, Inc. | Compositions for providing hydrophobic layers to metallic substrates |
| US20110195187A1 (en) * | 2010-02-10 | 2011-08-11 | Apple Inc. | Direct liquid vaporization for oleophobic coatings |
| JP5740607B2 (ja) * | 2011-02-23 | 2015-06-24 | 東海光学株式会社 | 光学製品の耐久性試験方法 |
| US8715779B2 (en) | 2011-06-24 | 2014-05-06 | Apple Inc. | Enhanced glass impact durability through application of thin films |
| US20140078658A1 (en) * | 2012-09-18 | 2014-03-20 | Joseph C. Rubin | Detection of oleophobic coating |
| EP3084483A1 (fr) | 2013-12-19 | 2016-10-26 | 3M Innovative Properties Company | Articles comprenant des couches autoassemblées contenant des nanoparticules avec un traitement de surface au phosphore |
| WO2016109203A2 (fr) * | 2014-12-29 | 2016-07-07 | 3M Innovative Properties Company | Articles revêtus et leurs procédés de fabrication |
Citations (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787351A (en) | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
| US4539061A (en) * | 1983-09-07 | 1985-09-03 | Yeda Research And Development Co., Ltd. | Process for the production of built-up films by the stepwise adsorption of individual monolayers |
| US5106561A (en) * | 1989-03-09 | 1992-04-21 | Nanofilm Corporation | Method of making film |
| US5139879A (en) | 1991-09-20 | 1992-08-18 | Allied-Signal Inc. | Fluoropolymer blend anti-reflection coatings and coated articles |
| US5166000A (en) * | 1991-10-10 | 1992-11-24 | Nanofilm Corporation | Method of applying thin films of amphiphilic molecules to substrates |
| US5204126A (en) * | 1990-02-06 | 1993-04-20 | Nanofilm Corporation | Mold surfaces with ultra thin release films |
| US5219654A (en) * | 1990-02-06 | 1993-06-15 | Nanofilm Corporation | Film forming composition and method for modifying surfaces with ultra thin films |
| US5392156A (en) | 1992-03-31 | 1995-02-21 | Canon Kabushiki Kaisha | Optical device |
| US5766698A (en) * | 1996-11-25 | 1998-06-16 | Nanofilm Corporation | Method for modifying surfaces with ultra thin films |
| US5846650A (en) | 1996-05-10 | 1998-12-08 | Minnesota Mining And Manufacturing Company | Anti-reflective, abrasion resistant, anti-fogging coated articles and methods |
| US6171652B1 (en) * | 1998-05-26 | 2001-01-09 | Brij P. Singh | Method for modifying surfaces with ultra thin films |
| US6395341B1 (en) * | 1998-07-17 | 2002-05-28 | Orient Chemical Industries, Ltd. | Organic-inorganic hybrid polymer materials with compositional gradient, and processes for preparing the same |
| US6455142B1 (en) | 1999-12-17 | 2002-09-24 | Mitsubishi Polyester Film, Llc | Anti-fog coating and coated film |
| US6645644B1 (en) * | 1996-10-17 | 2003-11-11 | The Trustees Of Princeton University | Enhanced bonding of phosphoric and phosphoric acids to oxidized substrates |
| US20040023048A1 (en) * | 1997-02-04 | 2004-02-05 | Jeffrey Schwartz | Enhanced bonding layers on native oxide surfaces |
| US6734227B2 (en) | 2001-09-24 | 2004-05-11 | 3M Innovative Properties Company | Optical elements comprising a fluoropolymer surface treatment |
| US6737145B1 (en) * | 1998-10-22 | 2004-05-18 | Ube Nitto Kasei Co., Ltd. | Organic-inorganic composite graded material, method for preparation thereof and use thereof |
| US6881445B1 (en) * | 2001-10-29 | 2005-04-19 | Innovation Chemical Technologies, Ltd. | Forming thin films on substrates using a porous carrier |
| US6890987B2 (en) * | 2000-10-18 | 2005-05-10 | Nanofilm, Ltd. | Product for vapor deposition of films of amphiphilic molecules or polymers |
| US6902791B2 (en) | 2001-06-25 | 2005-06-07 | Asahi Glass Company, Limited | Optical film |
| US6905754B2 (en) | 2002-04-26 | 2005-06-14 | 3M Innovative Properties Company | Optical elements comprising fluorochemical surface treatment |
| US6960387B2 (en) | 2001-06-25 | 2005-11-01 | Asahi Glass Company, Limited | Optical film |
| US6969166B2 (en) * | 2003-05-29 | 2005-11-29 | 3M Innovative Properties Company | Method for modifying the surface of a substrate |
| US7048971B2 (en) * | 2002-05-01 | 2006-05-23 | Innovation Chemical Technologies, Ltd. | Making invisible logos using hydrophobic and hydrophilic coatings |
| US20070092735A1 (en) * | 2005-10-24 | 2007-04-26 | Bruner Eric L | Polymeric organometallic films |
| US20080131701A1 (en) * | 2006-11-15 | 2008-06-05 | Hanson Eric L | Organometallic films, methods for applying organometallic films to substrates and substrates coated with such films |
| US20080248293A1 (en) * | 2007-04-04 | 2008-10-09 | Hanson Eric L | Inorganic substrates with hydrophobic surface layers |
| US7740940B2 (en) * | 2006-11-15 | 2010-06-22 | Aculon, Inc. | Coated substrates, organometallic films and methods for applying organometallic films to substrates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5126189A (en) * | 1987-04-21 | 1992-06-30 | Gelman Sciences, Inc. | Hydrophobic microporous membrane |
| US6582823B1 (en) * | 1999-04-30 | 2003-06-24 | North Carolina State University | Wear-resistant polymeric articles and methods of making the same |
| US6824882B2 (en) * | 2002-05-31 | 2004-11-30 | 3M Innovative Properties Company | Fluorinated phosphonic acids |
| EP1809706B1 (fr) * | 2004-10-22 | 2012-05-02 | ESSILOR INTERNATIONAL (Compagnie Générale d'Optique) | Substrat comprenant un revetement antisalissures |
-
2007
- 2007-08-24 US US11/895,484 patent/US8067103B2/en not_active Expired - Fee Related
- 2007-08-24 WO PCT/US2007/018751 patent/WO2008024475A2/fr active Application Filing
Patent Citations (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3787351A (en) | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
| US4539061A (en) * | 1983-09-07 | 1985-09-03 | Yeda Research And Development Co., Ltd. | Process for the production of built-up films by the stepwise adsorption of individual monolayers |
| US5106561A (en) * | 1989-03-09 | 1992-04-21 | Nanofilm Corporation | Method of making film |
| US5204126A (en) * | 1990-02-06 | 1993-04-20 | Nanofilm Corporation | Mold surfaces with ultra thin release films |
| US5219654A (en) * | 1990-02-06 | 1993-06-15 | Nanofilm Corporation | Film forming composition and method for modifying surfaces with ultra thin films |
| US5139879A (en) | 1991-09-20 | 1992-08-18 | Allied-Signal Inc. | Fluoropolymer blend anti-reflection coatings and coated articles |
| US5166000A (en) * | 1991-10-10 | 1992-11-24 | Nanofilm Corporation | Method of applying thin films of amphiphilic molecules to substrates |
| US5392156A (en) | 1992-03-31 | 1995-02-21 | Canon Kabushiki Kaisha | Optical device |
| US5846650A (en) | 1996-05-10 | 1998-12-08 | Minnesota Mining And Manufacturing Company | Anti-reflective, abrasion resistant, anti-fogging coated articles and methods |
| US6645644B1 (en) * | 1996-10-17 | 2003-11-11 | The Trustees Of Princeton University | Enhanced bonding of phosphoric and phosphoric acids to oxidized substrates |
| US5766698A (en) * | 1996-11-25 | 1998-06-16 | Nanofilm Corporation | Method for modifying surfaces with ultra thin films |
| US5897918A (en) * | 1996-11-25 | 1999-04-27 | Nanofilm, Ltd. | Method for modifying surfaces with ultra thin films |
| US20040023048A1 (en) * | 1997-02-04 | 2004-02-05 | Jeffrey Schwartz | Enhanced bonding layers on native oxide surfaces |
| US6171652B1 (en) * | 1998-05-26 | 2001-01-09 | Brij P. Singh | Method for modifying surfaces with ultra thin films |
| US6395341B1 (en) * | 1998-07-17 | 2002-05-28 | Orient Chemical Industries, Ltd. | Organic-inorganic hybrid polymer materials with compositional gradient, and processes for preparing the same |
| US6965001B2 (en) * | 1998-07-17 | 2005-11-15 | Orient Chemical Industries, Ltd. | Organic-inorganic hybrid polymer materials with compositional gradient, and processes for preparing the same |
| US6737145B1 (en) * | 1998-10-22 | 2004-05-18 | Ube Nitto Kasei Co., Ltd. | Organic-inorganic composite graded material, method for preparation thereof and use thereof |
| US6455142B1 (en) | 1999-12-17 | 2002-09-24 | Mitsubishi Polyester Film, Llc | Anti-fog coating and coated film |
| US6890987B2 (en) * | 2000-10-18 | 2005-05-10 | Nanofilm, Ltd. | Product for vapor deposition of films of amphiphilic molecules or polymers |
| US6902791B2 (en) | 2001-06-25 | 2005-06-07 | Asahi Glass Company, Limited | Optical film |
| US6960387B2 (en) | 2001-06-25 | 2005-11-01 | Asahi Glass Company, Limited | Optical film |
| US6734227B2 (en) | 2001-09-24 | 2004-05-11 | 3M Innovative Properties Company | Optical elements comprising a fluoropolymer surface treatment |
| US6881445B1 (en) * | 2001-10-29 | 2005-04-19 | Innovation Chemical Technologies, Ltd. | Forming thin films on substrates using a porous carrier |
| US6905754B2 (en) | 2002-04-26 | 2005-06-14 | 3M Innovative Properties Company | Optical elements comprising fluorochemical surface treatment |
| US7048971B2 (en) * | 2002-05-01 | 2006-05-23 | Innovation Chemical Technologies, Ltd. | Making invisible logos using hydrophobic and hydrophilic coatings |
| US6969166B2 (en) * | 2003-05-29 | 2005-11-29 | 3M Innovative Properties Company | Method for modifying the surface of a substrate |
| US20070092735A1 (en) * | 2005-10-24 | 2007-04-26 | Bruner Eric L | Polymeric organometallic films |
| US20080131701A1 (en) * | 2006-11-15 | 2008-06-05 | Hanson Eric L | Organometallic films, methods for applying organometallic films to substrates and substrates coated with such films |
| US7740940B2 (en) * | 2006-11-15 | 2010-06-22 | Aculon, Inc. | Coated substrates, organometallic films and methods for applying organometallic films to substrates |
| US7901777B2 (en) * | 2006-11-15 | 2011-03-08 | Aculon, Inc. | Coated substrates, organometallic films and methods for applying organometallic films to substrates |
| US20080248293A1 (en) * | 2007-04-04 | 2008-10-09 | Hanson Eric L | Inorganic substrates with hydrophobic surface layers |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US11718067B2 (en) | 2007-08-10 | 2023-08-08 | Greenhill Antiballistics Corporation | Composite material |
| US9060560B2 (en) | 2007-08-10 | 2015-06-23 | Greenhill Antiballistics Corporation | Composite material |
| US9982736B2 (en) | 2010-10-18 | 2018-05-29 | Greenhill Antiballistics Corporation | Gradient nanoparticle-carbon allotrope polymer composite |
| US9328788B2 (en) | 2010-10-18 | 2016-05-03 | Greenhill Antiballistics Corporation | Gradient nanoparticle-carbon allotrope-polymer composite material |
| US10926513B2 (en) | 2010-10-18 | 2021-02-23 | Greenhill Antiballistics Corporation | Gradient nanoparticle-carbon allotrope-polymer composite material |
| US9476754B2 (en) | 2013-02-28 | 2016-10-25 | Electrolab, Inc. | Method and kit for treatment of components utilized in a crude oil service operation |
| US10053640B2 (en) | 2013-02-28 | 2018-08-21 | Aculon Inc. | Method and kit for treatment of components utilized in a crude oil service operation |
| US10934497B2 (en) | 2013-02-28 | 2021-03-02 | E9 Treatments, Inc. | SAMP treatment method for a device utilized in a crude oil service operation, and method of installing said device |
| US9688926B2 (en) | 2013-02-28 | 2017-06-27 | Electrolab, Inc. | SAMP coated level sensor, method of treating a level sensor, and method of installing level sensor into crude oil service operation |
| US10150924B2 (en) | 2013-02-28 | 2018-12-11 | Electrolab, Inc. | Bonded layer treatment method for a device utilized in a crude oil service operation, and method of installing said device |
| US10059892B2 (en) | 2013-02-28 | 2018-08-28 | Electrolab, Inc. | SAMP coated cooperating surfaces, method of treating cooperating surfaces, and method of installing cooperating surfaces into crude oil service operation |
| US9421574B2 (en) | 2013-03-18 | 2016-08-23 | Aculon, Inc. | Fluorocarbon polymer coatings prepared by living polymerization |
| US9822621B2 (en) | 2013-09-20 | 2017-11-21 | Baker Hughes, A Ge Company, Llc | Method of using surface modifying treatment agents to treat subterranean formations |
| US9683431B2 (en) | 2013-09-20 | 2017-06-20 | Baker Hughes Incorporated | Method of using surface modifying metallic treatment agents to treat subterranean formations |
| US10047280B2 (en) | 2013-09-20 | 2018-08-14 | Baker Hughes, A Ge Company, Llc | Organophosphorus containing composites for use in well treatment operations |
| WO2015042486A1 (fr) | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Composites destinés à être utilisés dans des opérations de stimulation et de contrôle de sable |
| WO2015042488A2 (fr) | 2013-09-20 | 2015-03-26 | Baker Hughes Incorporated | Procédé permettant d'empêcher l'encrassement sur une surface métallique à l'aide d'un agent de traitement de modification de surface |
| US10227846B2 (en) | 2013-09-20 | 2019-03-12 | Baker Hughes, A Ge Company, Llc | Method of inhibiting fouling on a metallic surface using a surface modifying treatment agent |
| US9562188B2 (en) | 2013-09-20 | 2017-02-07 | Baker Hughes Incorporated | Composites for use in stimulation and sand control operations |
| US10039442B2 (en) | 2014-02-07 | 2018-08-07 | Sur-Seal Corporation | Anti-fog film for an endoscope |
| US9701892B2 (en) | 2014-04-17 | 2017-07-11 | Baker Hughes Incorporated | Method of pumping aqueous fluid containing surface modifying treatment agent into a well |
| US10647884B1 (en) | 2014-09-12 | 2020-05-12 | Newtech Llc | Polysilazane and fluoroacrylate coating composition |
| US9994732B1 (en) | 2014-09-12 | 2018-06-12 | Steven Martin Johnson | Polysilazane and fluoroacrylate coating composition |
| WO2016145263A1 (fr) | 2015-03-10 | 2016-09-15 | Baker Hughes Incorporated | Procédé de pompage d'un agent de traitement de modification de surface contenant un fluide aqueux dans un puits |
| US10562065B1 (en) | 2015-11-03 | 2020-02-18 | Newtech Llc | Systems and methods for application of polysilazane and fluoroacrylate coating compositions |
| US10584264B1 (en) | 2016-02-25 | 2020-03-10 | Newtech Llc | Hydrophobic and oleophobic coating compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080049326A1 (en) | 2008-02-28 |
| WO2008024475A2 (fr) | 2008-02-28 |
| WO2008024475A3 (fr) | 2008-07-10 |
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